CN101717353B - Synthesis method of taurine - Google Patents
Synthesis method of taurine Download PDFInfo
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- CN101717353B CN101717353B CN2009102129321A CN200910212932A CN101717353B CN 101717353 B CN101717353 B CN 101717353B CN 2009102129321 A CN2009102129321 A CN 2009102129321A CN 200910212932 A CN200910212932 A CN 200910212932A CN 101717353 B CN101717353 B CN 101717353B
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- taurine
- reaction
- bullion
- oxyethane
- ammonium
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Abstract
The invention relates to a synthesis method of taurine, belonging to the technical field of organic chemical synthesis. The synthesis method comprises the following steps of: reacting the oxirane with ammonium sulfite to obtain taurine ammonium salt, and acidating and refining to obtain the taurine. The reaction steps of the technical scheme are less, the taurine ammonium salt can be obtained just by one-step reaction between the oxirane and the ammonium sulfite, the crude taurine can be obtained by acidating, and the taurine is obtained by refining, therefore, the synthesis method has simple process and can embody the economical efficiency and the cleaning production.
Description
Technical field
The invention belongs to the organic chemistry synthesis technical field, be specifically related to a kind of compound method of taurine.
Background technology
Taurine (Taurine) claim taurocholic acid again, is a kind of sulfur-bearing nonprotein amino acid, chemistry 2-aminoethyl sulfonic acid (NH by name
2CH
2CH
2SO
3H), in recent years along with to the physiological action of taurine, the further investigation of nutritive value, its application is also more and more wider, at aspects such as medicine, food, tensio-active agent, pH buffer reagents important use is arranged all.Taurine can be used for cholagogic, protects the liver, detoxifcation, anti-inflammatory, analgesic, calm, anticonvulsion, anti-heart disorder, treatment Cardiac Insufficiency, regulates osmotic pressure, brings high blood pressure down, treats arteriosclerosis, suppresses nervus centralis and keep eyesight etc. as medicine.Present developed country has in the world added an amount of taurine like the U.S. and Japan in the milk of supplying with consumption by infants and milk powder, guarantee infant's health and normal development with this.There were many enterprises in China over the past two years from its attention to infant development, had developed a series of commodity that contain taurine.Modern study shows, taurine has the effect of a series of uniquenesses to adult cardiovascular systems, have build up health, preventing disease, relieving fatigue and the effect of improving work efficiency.
Taurine is since finding, people are just constantly exploring the approach of its synthetic.So far; About the compound method of taurine has down tens of kinds of dichloroethane law, epoxyethane method and thanomin sulfuric ester reduction methods etc.; Chinese invention patent application publication number CN101100449A discloses a kind of compound method (the applicant's application) of taurine, and it is, and to be reductive agent with the sulfurous acid ammonium salt carry out reduction reaction to the carboxylate of thanomin, obtains bullion through separating; Recrystallization obtains the finished product taurine again.The technique effect of this patented claim scheme can be isolated taurine and vitriol at low temperatures, does not have SO in the production process
2Gas escapes, and production environment is friendly.But this method is difficult control in actual production process, and reaction is a starting raw material with the Monoethanolamine MEA BASF, through salify, esterification, reduction with make with extra care and accomplish, and Monoethanolamine MEA BASF be by oxyethane through high pressure ammonification gained, technology is cumbersome, raw materials cost is expensive.Therefore, be necessary the compound method of the taurine in the prior art is improved, use the not only simple and easy to do but also economic and reliable of embodiment and can embody cleaning production.
Summary of the invention
Task of the present invention is to provide a kind of and had both helped to reduce reactions step and simplified technology, the compound method that helps again embodying economy He clean the taurine of production.
Task of the present invention is accomplished like this, a kind of compound method of taurine, and it is that oxyethane and ammonium sulphite reaction are obtained the taurine ammonium salt, with refining, obtains taurine through acidifying.
Oxyethane of the present invention is 1: 0.5～2 with ammonium sulphite mixing molar ratio.
Oxyethane of the present invention and ammonium sulphite reaction are under the normal pressure or greater than normal pressure any one reaction of reaction down.
Oxyethane of the present invention and ammonium sulphite temperature of reaction are 100～300 ℃.
Oxyethane of the present invention and ammonium sulphite temperature of reaction are 150～220 ℃.
Technical scheme reactions step provided by the invention is few; Oxyethane and ammonium sulphite only single step reaction just obtain the taurine ammonium salt; Get the taurine bullion through acidifying, refining must taurine, so technology is terse and can embody economy and can embody and clean production.
Embodiment:
Embodiment 1:
In the stainless steel autoclave that 1000 liters of bands stir, heat, install, put into 200 kg of water, and add ammonium sulphite (80.0%) 145 kilogram (1 * 10
3Mol), under agitation feed oxyethane (99.9%) 44 kilogram (1.0 * 10
3Mol), then heated sealed, be stirred to 150 ℃～160 ℃ of temperature in the kettle, and to keep the still internal pressure be 0.5-1MPa; And continue between reaction 5 hours; Get the taurine ammonium salt solution, and under agitation cool to below 50 ℃, add 50% sulfuric acid and regulate material pH value in the still≤7; Spinning gets 130 kilograms of bullion taurines;
130 kilograms of above-mentioned bullion taurines are dropped in the reaction kettle of 500L; Add water 200L and 0.1 kilogram of activated carbon; Under heating, stirring, make the dissolving of bullion taurine, filtering to remove activated carbon gets colourless transparent liquid excessively, under agitation cools to 5 ℃; Spinning and wash 95 kilograms of elaboration taurines, 90 kilogram (0.720 * 10 of dry finished product taurine
3Mol), yield is 72.0%, and through detecting, taurine master content is 99.83%, and all other indexs all meet JP8 and USP26.The chemical equation of present embodiment is following:
The first step reaction synthesized taurine ammonium salt:
Taurine is produced in the second sour regurgitation reaction:
2NH
2CH
2CH
2SO
3NH
4+H
2SO
4→2NH
2CH
2CH
2SO
3H+(NH
4)
2SO
4
Embodiment 2:
In the four-hole boiling flask that 1000 milliliters of bands stir, heat, install, put into 200 gram water; And add ammonium sulphite (80.0%) 290 gram (2mol), and under agitation feeding oxyethane (99.9%) 44 gram (1mol), 100 ℃～115 ℃ of temperature in the kettle are heated, are stirred in water seal then; And keep the flask internal pressure be under the normal pressure reaction 5 hours; Get the taurine ammonium salt solution, and under agitation cool to below 50 ℃, add 50% sulfuric acid and regulate material pH value in the still≤7; Spinning gets bullion taurine 121 grams;
Above-mentioned bullion taurine 121 grams are dropped in the four-hole boiling flask of 500 milliliters of band stirrings, heating, device; Add water 200 grams and 0.1 gram activated carbon; Under heating, stirring, make the dissolving of bullion taurine, filtering to remove activated carbon gets colourless transparent liquid excessively, under agitation cools to 5 ℃; Spinning and wash elaboration taurine 91 gram, dry finished product taurine 86 grams (0.688 * 10
3Mol), yield is 68.8%, and through detecting, taurine master content is 99.86%, and all other indexs all meet JP8 and USP26.Chemical equation is with embodiment 1.
Embodiment 3:
In the four-hole boiling flask that 1000 milliliters of bands stir, heat, install, put into 200 gram water, and add ammonium sulphite (80.0%) 145 gram (1mol), under agitation feed oxyethane (99.9%) 88 and restrain (2mol); 105 ℃～100 ℃ of bottle interior temperature are heated, are stirred in water seal then, and normal pressure reacted 5 hours down, got the taurine ammonium salt solution; And under agitation cool to below 50 ℃; Add 30% sulfuric acid and regulate material pH value in the still≤7, spinning gets bullion taurine 129 grams;
Above-mentioned bullion taurine 129 grams are dropped in the four-hole boiling flask of 500 milliliters of band stirrings, heating, device; Add water 200 grams and 0.1 gram activated carbon; Under heating, stirring, make the dissolving of bullion taurine, filtering to remove activated carbon gets colourless transparent liquid excessively, under agitation cools to 5 ℃; Spinning and wash elaboration taurine 93 gram, dry finished product taurine 88 grams (0.704 * 10
3Mol), yield is 70.4%, and through detecting, taurine master content is 99.91%, and all other indexs all meet JP8 and USP26.Chemical equation is with embodiment 1.
Embodiment 4:
In the glassed steel reaction vessels that 1000 liters of bands stir, heat, install, put into 200 kg of water, and add ammonium sulphite (80.0%) 217.5 kilogram (1.5 * 10
3Mol), under agitation feed oxyethane (99.9%) 44 kilogram (1.0 * 10
3Mol), then heated sealed, be stirred to 150 ℃～155 ℃ of temperature in the kettle, and to keep the still internal pressure be 0.3-0.5MPa; And continue between reaction 5 hours; Get the taurine ammonium salt solution, and under agitation cool to below 50 ℃, add 60% sulfuric acid and regulate material pH value in the still≤7; Spinning gets 141 kilograms of bullion taurines;
141 kilograms of above-mentioned bullion taurines are dropped in the reaction kettle of 500L; Add water 200L and 0.1 kilogram of activated carbon; Under heating, stirring, make the dissolving of bullion taurine, filtering to remove activated carbon gets colourless transparent liquid excessively, under agitation cools to 5 ℃; Spinning and wash 96 kilograms of elaboration taurines, 91 kilogram (0.728 * 10 of dry finished product taurine
3Mol), yield is 72.8%, and through detecting, taurine master content is 99.87%, and all other indexs all meet JP8 and USP26.Chemical equation is with embodiment 1.
Embodiment 5:
In the stainless steel autoclave that 1000 liters of bands stir, heat, install, put into 200 kg of water, and add ammonium sulphite (80.0%) 145 kilogram (1 * 10
3Mol), under agitation feed oxyethane (99.9%) 66 kilogram (1.5 * 10
3Mol), then heated sealed, be stirred to 295 ℃～300 ℃ of temperature in the kettle, and to keep the still internal pressure be 20-25MPa; And continue between reaction 5 hours; Under agitation cool to below 50 ℃, get the taurine ammonium salt solution, and add material pH value≤7 in the 50% sulfuric acid adjusting still; Spinning gets 137 kilograms of bullion taurines;
137 kilograms of above-mentioned bullion taurines are dropped in the reaction kettle of 500L; Add water 200L and 0.1 kilogram of activated carbon; Under heating, stirring, make the dissolving of bullion taurine, filtering to remove activated carbon gets colourless transparent liquid excessively, under agitation cools to 5 ℃; Spinning and wash 93 kilograms of elaboration taurines, 89 kilogram (0.712 * 10 of dry finished product taurine
3Mol), yield is 71.2%, and through detecting, taurine master content is 99.94%, and all other indexs all meet JP8 and USP26.Chemical equation is with embodiment 1.
Embodiment 6:
In the stainless steel autoclave that 1000 liters of bands stir, heat, install, put into 200 kg of water, and add ammonium sulphite (80.0%) 145 kilogram (1 * 10
3Mol), under agitation feed oxyethane (99.9%) 44 kilogram (1.0 * 10
3Mol), then heated sealed, be stirred to 200 ℃～205 ℃ of temperature in the kettle, and to keep the still internal pressure be 8-12MPa; And continue between reaction 2 hours; Get the taurine ammonium salt solution, and under agitation cool to below 30 ℃, add 50% sulfuric acid and regulate material pH value in the still≤7; Spinning gets 143 kilograms of bullion taurines;
143 kilograms of above-mentioned bullion taurines are dropped in the reaction kettle of 500L; Add water 200L and 0.1 kilogram of activated carbon; Under heating, stirring, make the dissolving of bullion taurine, filtering to remove activated carbon gets colourless transparent liquid excessively, under agitation cools to 5 ℃; Spinning and wash elaboration taurine 105 kg, 98 kilogram (0.784 * 10 of dry finished product taurine
3Mol), yield is 78.4%, and through detecting, taurine master content is 99.81%, and all other indexs all meet JP8 and USP26.Chemical equation is with embodiment 1
Claims (4)
1. the compound method of a taurine is characterized in that it is that oxyethane and ammonium sulphite reaction are obtained the taurine ammonium salt, with refining, obtains taurine through acidifying, and described oxyethane and ammonium sulphite temperature of reaction are 100～300 ℃.
2. the compound method of taurine according to claim 1 is characterized in that described oxyethane is 1: 0.5～2 with ammonium sulphite mixing molar ratio.
3. the compound method of taurine according to claim 1 is characterized in that the reaction of described oxyethane and ammonium sulphite is under the normal pressure or greater than normal pressure any one reaction of reaction down.
4. the compound method of taurine according to claim 1 is characterized in that described oxyethane and ammonium sulphite temperature of reaction are 150～220 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102129321A CN101717353B (en) | 2009-11-11 | 2009-11-11 | Synthesis method of taurine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102129321A CN101717353B (en) | 2009-11-11 | 2009-11-11 | Synthesis method of taurine |
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|---|---|
| CN101717353A CN101717353A (en) | 2010-06-02 |
| CN101717353B true CN101717353B (en) | 2012-06-27 |
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|---|---|---|---|
| CN2009102129321A Expired - Fee Related CN101717353B (en) | 2009-11-11 | 2009-11-11 | Synthesis method of taurine |
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Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101851182B (en) * | 2010-06-03 | 2013-07-17 | 北京化工大学 | Salt-free preparation method for substituted taurine |
| US20210179551A1 (en) | 2014-04-18 | 2021-06-17 | Vitaworks Ip, Llc | Process for producing alkali taurinate |
| USRE48392E1 (en) | 2014-04-18 | 2021-01-12 | Vitaworks Ip, Llc | Cyclic process for the production of taurine from alkali isethionate |
| US9573890B2 (en) | 2014-04-18 | 2017-02-21 | Vitaworks Ip, Llc | Process for producing taurine |
| USRE48369E1 (en) | 2014-04-18 | 2020-12-29 | Vitaworks Ip, Llc | Process for producing taurine |
| US9428450B2 (en) | 2014-04-18 | 2016-08-30 | Songzhou Hu | Process for producing taurine from alkali taurinates |
| US9745258B1 (en) | 2016-09-16 | 2017-08-29 | Vitaworks Ip, Llc | Cyclic process for producing taurine |
| US10112894B2 (en) | 2016-09-16 | 2018-10-30 | Vitaworks Ip, Llc | Cyclic process for producing taurine |
| US9815778B1 (en) | 2016-09-16 | 2017-11-14 | Vitaworks Ip, Llc | Cyclic process for producing taurine |
| US10683264B2 (en) | 2016-09-16 | 2020-06-16 | Vitaworks Ip, Llc | Process for producing taurine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004113391A2 (en) * | 2003-06-23 | 2004-12-29 | Neurochem (International) Limited | Improved pharmaceutical drug candidates and methods for preparation thereof |
| CN101508657A (en) * | 2008-02-14 | 2009-08-19 | 王代龙 | Synthesis of taurine |
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2009
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004113391A2 (en) * | 2003-06-23 | 2004-12-29 | Neurochem (International) Limited | Improved pharmaceutical drug candidates and methods for preparation thereof |
| CN101508657A (en) * | 2008-02-14 | 2009-08-19 | 王代龙 | Synthesis of taurine |
Non-Patent Citations (2)
| Title |
|---|
| 吴江 等.牛磺酸生产工艺中氨解反应条件的优化.《湖北工学院学报》.2004,第19卷(第1期),第23-26页. * |
| 崔建兰等.牛磺酸的研究进展.《华北工学院学报》.1998,第19卷(第1期),第49-51页. * |
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| CN101717353A (en) | 2010-06-02 |
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Owner name: JIANGSU YUANYANG PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: JIANGSU YUANYANG CHEMICAL CO., LTD. Effective date: 20120329 |
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Effective date of registration: 20120329 Address after: 215531, Jiangsu, Changshou City province Tong Industrial Park, 204 National Road, 948.5 kilometers Applicant after: Jiangsu Yuanyang Pharmaceutical Co.,Ltd. Address before: 215531, Jiangsu, Changshou City province Tong Industrial Park, 204 National Road, 934.5 kilometers Applicant before: Jiangsu Yuanyang Chemical Co., Ltd. |
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